Imidazole → HCID 21270026, compound

HRID 1194354Notes

Reaction equation

HRID 1194354 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16](=[O:19])[CH:17]=[CH2:18])=[CH:8]1>C(OCC)(=O)C>[N:1]1([CH2:18][CH2:17][C:16]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([CH3:6])[CH:8]=2)=[O:19])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 129965751-(1-Methyl-1H-indol-3-yl)prop-2-en-1-one

Product 1

HCID 21270026HCID 21270026, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (0.433 g) was added to a solution of 1-(1-methyl-1H-indol-3-yl)-1-prop-2-enone (0.393 g) in ethyl acetate (12 ml) and the mixture was stirred and heated at reflux for 2.25 h. The mixture was cooled and allowed to stand for 18 h at room temperature. The resulting precipitate was filtered off, washed with ethyl acetate (2 ml) and ether (10 ml) and dried to give the title compound (0.317 g), m.p. 121°-123°; λmax (EtOH) 245.5 nm (ε14,080), λinf 248 nm (ε13,750), λinf 258 nm (ε9,400), λmax 304 nm (ε14,000).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.25 h
  3. temperatureThe mixture was cooled
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with ethyl acetate (2 ml) and ether (10 ml)
  6. customdried

Sources & evidence

ORD record
ord-9780b280843d4b8eafd204c0811deb27
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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